EP0372504B1 - Verfahren zur Herstellung einer positiven Photolackzusammensetzung - Google Patents

Verfahren zur Herstellung einer positiven Photolackzusammensetzung Download PDF

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Publication number
EP0372504B1
EP0372504B1 EP89122452A EP89122452A EP0372504B1 EP 0372504 B1 EP0372504 B1 EP 0372504B1 EP 89122452 A EP89122452 A EP 89122452A EP 89122452 A EP89122452 A EP 89122452A EP 0372504 B1 EP0372504 B1 EP 0372504B1
Authority
EP
European Patent Office
Prior art keywords
condensation reaction
quinone diazide
positive resist
solution
solvent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Revoked
Application number
EP89122452A
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English (en)
French (fr)
Other versions
EP0372504A1 (de
Inventor
Takeshi Hioki
Koji Kuwana
Jun Tomioka
Hirotoshi Nakanishi
Yasunori Uetani
Yukio Hanamoto
Fumio 3-15-506 Hamaashiya-Cho Oi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of EP0372504A1 publication Critical patent/EP0372504A1/de
Application granted granted Critical
Publication of EP0372504B1 publication Critical patent/EP0372504B1/de
Anticipated expiration legal-status Critical
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders

Definitions

  • the present invention relates to a process for preparing a positive resist composition including a quinone diazide compound.
  • Positive resist compositions comprising an alkali-soluble resin and a quinone diazide compound are used in the production of integrated circuits by photographic etching.
  • positive resist compositions have been prepared by mixing an isolated quinone diazide sulfonic ester with an alkali-soluble resin, a resist solution and so on. Namely, a quinone diazide sulfonyl halogenide undergoes a condensation reaction with a phenol compound in the presence of an alkali in a polar organic solvent such as dioxane, methyl ethyl ketone or mixtures thereof.
  • a quinone diazide sulfonyl halogenide undergoes a condensation reaction with a phenol compound in the presence of an alkali in a polar organic solvent such as dioxane, methyl ethyl ketone or mixtures thereof.
  • Another process comprises adding a resist solvent to the resulting solution from the condensation reaction without precipitation, filtering or drying, then removing the impurities from the mixture and recovering a solution of the quinone diazide sulfonyl ester in the resist solvent.
  • a resist solvent to the resulting solution from the condensation reaction without precipitation, filtering or drying, then removing the impurities from the mixture and recovering a solution of the quinone diazide sulfonyl ester in the resist solvent.
  • EP-A-0 244 762 relates to a positive light-resistive mixture obtainable by reacting a phenol and a quinone diazide sulfonyl chloride, subjecting this product to filtration for isolation and mixing the isolated product with a novalak resin and PEMEA and a solvent.
  • FR-A-2 173 074 relates to a product obtainable by reacting a polymeric amine and a quinone diazide sulfonyl chloride and isolating this compound which is thereafter mixed with a resin and a solvent.
  • the object of the present invention is to provide a The object of the present invention is to provide a process for preparing a positive resist composition in a short processing time.
  • the present invention provides a process for preparing a positive resist composition, which process comprises the steps of condensation reaction of a quinone diazide sulfonyl halogenide with a phenol compound, mixingthecondensation reaction mixture with a solution of an alkali-soluble resin in a resist solvent and removing impurities including the solvent used in the condensation reaction from the mixture.
  • the quinone diazide sulfonyl halogenide is condensation reacted with the phenol compound in a solvent to obtain a solution of the quinone diazide sulfonyl ester.
  • phenol compound examples include (poly)hydroxybenzenes (e.g. cresol and resorcinol), (poly)hydroxyphenyl alkyl ketones (e.g. 2,4-dihydroxyphenyl propyl ketone), (poly)hydroxyphenyl aryl ketones (e.g. 2,3,4-trihydroxybenzophenone and 2,3,4,4'-tetrahydroxybenzophenone), bis-[(poly)hydroxyphenyl]alkanes (e.g. 2,2-bis(2,4-dihydroxyphenyl)propane) and (poly)hydroxyphenyl aryl alkanes (e.g. 2-(4-hydroxyphenyl)-2-(2,4-dihydroxyphenyl)propane).
  • polyhydroxybenzenes e.g. cresol and resorcinol
  • poly)hydroxyphenyl alkyl ketones e.g. 2,4-dihydroxyphenyl propyl ketone
  • poly hydroxypheny
  • polar organic solvents are preferably used.
  • Such solvents include dioxane, methyl ethyl ketone, cyclohexanone or y-butyrolactone. These solvents may be used alone or in combination.
  • quinone diazide sulfonyl ester examples include 1,2-benzoquinone diazide-4-sulfonyl ester, 1,2-naphthoquinone diazide-4-sulfonyl ester and 1,2-naphthoquinone diazide-5-sulfonyl ester.
  • Themolar ratio of the phenol compound to the quinone diazide sulfonyl halogenide is preferably from 1:1 to 1:4.
  • the condensation reaction can be carried out in the presence of a base catalyst.
  • the base catalysts are amines such as triethyl amine, inorganic bases such as sodium hydroxide, sodium carbonate and sodium hydrogencarbonate, and mixtures thereof.
  • the amount of the base catalyst is from 1 to 1.5 moles per one mole of the quinone diazide sulfonyl halogenide.
  • the solution of the quinone diazide sulfonyl ester is mixed with the solution of the alkali-soluble resin in the resist solvent.
  • the weight ratio of the quinone diazide sulfonyl ester to the alkali-soluble resin is preferably from 1:1 to 1:1.5.
  • a novolak resin is preferably used as the alkali-soluble resin.
  • the novolak resins are prepared by a condensation reaction of a phenol compound (e.g. phenol and cresol) with formaldehyde such as formalin.
  • resist solvent examples include ethyl cellosolve acetate, methyl cellosolve acetate, ethyl cellosolve, methyl cellosolve, propyleneglycolmonomethylether acetate, butyl acetate, methyl isobutyl ketone and xylene.
  • the concentration of the alkali-soluble resin in the resist solvent is preferably from 10 to 60 % by weight.
  • impurities such as the solvent used in the condensation reaction are removed from the solution containing the alkali-soluble resin and the quinone diazide sulfonyl ester.
  • the solvent can be removed by evaporation.
  • the salts by-produced through the condensation reaction are removed by filtration.
  • the salts of other metals may be removed by washing with water. Water can be also removed by evaporation.
  • the positive resists are prepared by controllingthe concentration of the solution without impurity, if necessary and filtrating the solution to remove minute dusts.
  • filtration or drying step can be omitted and the processing time can be shortened.
  • the overall processing time was 10 hours.
  • the reaction solution was filtered to obtain a cake of quinone diazide sulfonyl ester.
  • the cake was washed with 600 g of ion exchanged water three times and dried for 50 hours at 40 °C to obtain a dry cake.
  • 129.4 g of the dry cake 1157.8 g of a solution of cresol novolak resin in ethyl cellosolve acetate (weight average molecular weight of the novolak resin: 9000; and concentration: 35.0 %) and 651.5 g of ethyl cellosolve acetate was mixed.
  • the mixed resist solution was filtered through a Teflon (Trade mark) filter of 0.2 ⁇ m in pore size to obtain a positive resist solution.
  • the overall processing time was 58 hours.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Materials For Photolithography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Claims (3)

  1. Verfahren zur Herstellung einer positiven Resistzusammensetzung, wobei das Verfahren die Schritte
    (a) Umsetzung eines Chinondiazidsulfonsäurehalogenids mit einer Phenolverbindung durch Kondensation,
    (b) Mischen des Kondensationsreaktionsgemisches mit einer Lösung eines basenlöslichen Harzes in einem Resistlösungsmittel und
    (c) Entfernen von Verunreinigungen einschließlich des für die Kondensationsreaktion verwendeten Lösungsmittels aus dem Gemisch
    umfaßt.
  2. Verfahren zur Herstellung einer positiven Resistzusammensetzung nach Anspruch 1, wobei das basenlösliche Harz ein Novolakharz ist.
  3. Verfahren zur Herstellung einer positiven Resistzusammensetzung, wobei das Verfahren die Schritte
    (a) Umsetzung eines Chinondiazidsulfonsäurehalogenids mit einer Phenolverbindung durch Kondensation,
    (b) Entfernen von Salz, das als Nebenprodukt bei der Kondensationsreaktion gebildet wird, durch Filtration,
    (c) Mischen des Kondensationsreaktionsgemisches mit einer Lösung eines basenlöslichen Harzes in einem Resistlösungsmittel und
    (d) Entfernen von Verunreinigungen einschließlich des für die Kondensationsreaktion verwendeten Lösungsmittels aus dem Gemisch
    umfaßt.
EP89122452A 1988-12-06 1989-12-06 Verfahren zur Herstellung einer positiven Photolackzusammensetzung Revoked EP0372504B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP63308559A JP2697039B2 (ja) 1988-12-06 1988-12-06 ポジ型レジスト組成物の製造方法
JP308559/88 1988-12-06

Publications (2)

Publication Number Publication Date
EP0372504A1 EP0372504A1 (de) 1990-06-13
EP0372504B1 true EP0372504B1 (de) 1996-04-03

Family

ID=17982489

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89122452A Revoked EP0372504B1 (de) 1988-12-06 1989-12-06 Verfahren zur Herstellung einer positiven Photolackzusammensetzung

Country Status (7)

Country Link
US (1) US5080997A (de)
EP (1) EP0372504B1 (de)
JP (1) JP2697039B2 (de)
KR (1) KR0137764B1 (de)
CA (1) CA2004593A1 (de)
DE (1) DE68926151T2 (de)
MX (1) MX171835B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5300396A (en) * 1990-11-28 1994-04-05 Hoechst Celanese Corporation Process of making naphthoquinone diazide esters using lactone solvents
JP2976597B2 (ja) * 1991-04-17 1999-11-10 住友化学工業株式会社 キノンジアジドスルホン酸エステルの製造方法
US5618655A (en) * 1995-07-17 1997-04-08 Olin Corporation Process of reducing trace levels of metal impurities from resist components
US5623042A (en) * 1995-07-19 1997-04-22 Olin Corporation Process for reducing trace levels of metallic impurities in cyclized polyisoprene resin
US7015291B2 (en) 2002-04-01 2006-03-21 Daicel Chemical Industries, Ltd. Process for the production of high-molecular compounds for photoresist
US20060172231A1 (en) * 2002-08-08 2006-08-03 Fujifilm Electronic Materials U.S.A., Inc Use of an oxidizer to improve trace metals removal from photoresist and photoresist components
WO2004112581A2 (en) * 2003-06-18 2004-12-29 The Board Of Trustees Of The Leland Stanford Junior University Electro-adhesive tissue manipulator
JP4699482B2 (ja) * 2005-02-02 2011-06-08 コーロン インダストリーズ インク ポジティブ型ドライフィルムフォトレジストの製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0244762A2 (de) * 1986-05-02 1987-11-11 Hoechst Celanese Corporation Positiv-arbeitendes lichtempfindliches Gemisch und daraus hergestelltes lichtempfindliches Aufzeichnungsmaterial

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE795809A (fr) * 1972-02-22 1973-08-22 Eastman Kodak Co Nouveaux polymeres photosensibles a groupes o-quinone diazide
DE3100077A1 (de) * 1981-01-03 1982-08-05 Hoechst Ag, 6000 Frankfurt Lichtempfindliches gemisch, das einen naphthochinondiazidsulfonsaeureester enthaelt, und verfahren zur herstellung des naphthochinondiazidsulfonsaeureesters
JPS58205147A (ja) * 1982-05-25 1983-11-30 Sumitomo Chem Co Ltd ポジ型フオトレジスト組成物
US4550069A (en) * 1984-06-11 1985-10-29 American Hoechst Corporation Positive photoresist compositions with o-quinone diazide, novolak, and propylene glycol alkyl ether acetate
JPS61118744A (ja) * 1984-11-15 1986-06-06 Tokyo Ohka Kogyo Co Ltd ポジ型ホトレジスト組成物
JPS61185741A (ja) * 1985-02-13 1986-08-19 Mitsubishi Chem Ind Ltd ポジ型フオトレジスト組成物
JPH0654384B2 (ja) * 1985-08-09 1994-07-20 東京応化工業株式会社 ポジ型ホトレジスト組成物
JPS63178228A (ja) * 1987-01-20 1988-07-22 Fuji Photo Film Co Ltd ポジ型フオトレジスト組成物
JP2560266B2 (ja) * 1987-03-25 1996-12-04 日本合成ゴム株式会社 感放射線性樹脂組成物
JPS63305348A (ja) * 1987-06-05 1988-12-13 Fuji Photo Film Co Ltd ポジ型フオトレジスト組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0244762A2 (de) * 1986-05-02 1987-11-11 Hoechst Celanese Corporation Positiv-arbeitendes lichtempfindliches Gemisch und daraus hergestelltes lichtempfindliches Aufzeichnungsmaterial

Also Published As

Publication number Publication date
US5080997A (en) 1992-01-14
MX171835B (es) 1993-11-18
DE68926151D1 (de) 1996-05-09
KR900010465A (ko) 1990-07-07
DE68926151T2 (de) 1996-08-22
JPH02154259A (ja) 1990-06-13
CA2004593A1 (en) 1990-06-06
JP2697039B2 (ja) 1998-01-14
KR0137764B1 (ko) 1998-04-27
EP0372504A1 (de) 1990-06-13

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